WO2017016630A1 - Materials for organic electroluminescent devices - Google Patents
Materials for organic electroluminescent devices Download PDFInfo
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- WO2017016630A1 WO2017016630A1 PCT/EP2016/001117 EP2016001117W WO2017016630A1 WO 2017016630 A1 WO2017016630 A1 WO 2017016630A1 EP 2016001117 W EP2016001117 W EP 2016001117W WO 2017016630 A1 WO2017016630 A1 WO 2017016630A1
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- 239000000463 material Substances 0.000 title description 42
- 150000001875 compounds Chemical class 0.000 claims abstract description 123
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 40
- 125000003983 fluorenyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims abstract description 31
- 239000011159 matrix material Substances 0.000 claims abstract description 30
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 19
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 18
- 125000004306 triazinyl group Chemical group 0.000 claims abstract description 17
- 125000003118 aryl group Chemical group 0.000 claims description 76
- 125000001424 substituent group Chemical group 0.000 claims description 28
- 239000000203 mixture Substances 0.000 claims description 21
- 229920000642 polymer Polymers 0.000 claims description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 12
- 239000000412 dendrimer Substances 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 12
- 229920000736 dendritic polymer Polymers 0.000 claims description 11
- 229910052740 iodine Inorganic materials 0.000 claims description 11
- 239000004305 biphenyl Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 230000008569 process Effects 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 125000000304 alkynyl group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 9
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical compound C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 125000002950 monocyclic group Chemical group 0.000 claims description 8
- 125000003367 polycyclic group Chemical group 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- IYYZUPMFVPLQIF-UHFFFAOYSA-N dibenzothiophene Chemical compound C1=CC=C2C3=CC=CC=C3SC2=C1 IYYZUPMFVPLQIF-UHFFFAOYSA-N 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- 125000004104 aryloxy group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000004001 thioalkyl group Chemical group 0.000 claims description 6
- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 5
- 125000005580 triphenylene group Chemical group 0.000 claims description 5
- VIJYEGDOKCKUOL-UHFFFAOYSA-N 9-phenylcarbazole Chemical compound C1=CC=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 VIJYEGDOKCKUOL-UHFFFAOYSA-N 0.000 claims description 4
- SLGBZMMZGDRARJ-UHFFFAOYSA-N Triphenylene Natural products C1=CC=C2C3=CC=CC=C3C3=CC=CC=C3C2=C1 SLGBZMMZGDRARJ-UHFFFAOYSA-N 0.000 claims description 4
- 230000008878 coupling Effects 0.000 claims description 4
- 238000010168 coupling process Methods 0.000 claims description 4
- 238000005859 coupling reaction Methods 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000520 N-substituted aminocarbonyl group Chemical group [*]NC(=O)* 0.000 claims description 2
- 238000006619 Stille reaction Methods 0.000 claims description 2
- 238000006887 Ullmann reaction Methods 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 2
- 238000006880 cross-coupling reaction Methods 0.000 claims description 2
- 230000005669 field effect Effects 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 230000003287 optical effect Effects 0.000 claims description 2
- 108091008695 photoreceptors Proteins 0.000 claims description 2
- 238000010791 quenching Methods 0.000 claims description 2
- 239000010409 thin film Substances 0.000 claims description 2
- ICPSWZFVWAPUKF-UHFFFAOYSA-N 1,1'-spirobi[fluorene] Chemical class C1=CC=C2C=C3C4(C=5C(C6=CC=CC=C6C=5)=CC=C4)C=CC=C3C2=C1 ICPSWZFVWAPUKF-UHFFFAOYSA-N 0.000 abstract description 3
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 93
- -1 4- triazinyl Chemical group 0.000 description 55
- 101100533558 Mus musculus Sipa1 gene Proteins 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 19
- 150000003254 radicals Chemical class 0.000 description 16
- 125000001072 heteroaryl group Chemical group 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 150000001721 carbon Chemical group 0.000 description 8
- 238000002347 injection Methods 0.000 description 8
- 239000007924 injection Substances 0.000 description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 230000006872 improvement Effects 0.000 description 7
- 125000005647 linker group Chemical group 0.000 description 7
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 6
- 235000010290 biphenyl Nutrition 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 6
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 6
- SNFCXVRWFNAHQX-UHFFFAOYSA-N 9,9'-spirobi[fluorene] Chemical class C12=CC=CC=C2C2=CC=CC=C2C21C1=CC=CC=C1C1=CC=CC=C21 SNFCXVRWFNAHQX-UHFFFAOYSA-N 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 5
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 5
- 230000005525 hole transport Effects 0.000 description 5
- 238000007639 printing Methods 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 150000003230 pyrimidines Chemical class 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 238000000151 deposition Methods 0.000 description 4
- 230000008021 deposition Effects 0.000 description 4
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 4
- 229930192474 thiophene Natural products 0.000 description 4
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 3
- BKQXUNGELBDWLS-UHFFFAOYSA-N 9,9-diphenylfluorene Chemical compound C1=CC=CC=C1C1(C=2C=CC=CC=2)C2=CC=CC=C2C2=CC=CC=C21 BKQXUNGELBDWLS-UHFFFAOYSA-N 0.000 description 3
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 238000005401 electroluminescence Methods 0.000 description 3
- WUNJCKOTXFSWBK-UHFFFAOYSA-N indeno[2,1-a]carbazole Chemical compound C1=CC=C2C=C3C4=NC5=CC=CC=C5C4=CC=C3C2=C1 WUNJCKOTXFSWBK-UHFFFAOYSA-N 0.000 description 3
- VVVPGLRKXQSQSZ-UHFFFAOYSA-N indolo[3,2-c]carbazole Chemical compound C1=CC=CC2=NC3=C4C5=CC=CC=C5N=C4C=CC3=C21 VVVPGLRKXQSQSZ-UHFFFAOYSA-N 0.000 description 3
- 229910010272 inorganic material Inorganic materials 0.000 description 3
- 229910052741 iridium Inorganic materials 0.000 description 3
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000758 substrate Substances 0.000 description 3
- YKCZGQXLXXMGNR-UHFFFAOYSA-N (9,9-dimethylfluoren-4-yl)boronic acid Chemical compound C1=CC=C(B(O)O)C2=C1C(C)(C)C1=CC=CC=C12 YKCZGQXLXXMGNR-UHFFFAOYSA-N 0.000 description 2
- BFIMMTCNYPIMRN-UHFFFAOYSA-N 1,2,3,5-tetramethylbenzene Chemical compound CC1=CC(C)=C(C)C(C)=C1 BFIMMTCNYPIMRN-UHFFFAOYSA-N 0.000 description 2
- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
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- 125000005244 neohexyl group Chemical group [H]C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- VXNSQGRKHCZUSU-UHFFFAOYSA-N octylbenzene Chemical compound [CH2]CCCCCCCC1=CC=CC=C1 VXNSQGRKHCZUSU-UHFFFAOYSA-N 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
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- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- SLIUAWYAILUBJU-UHFFFAOYSA-N pentacene Chemical compound C1=CC=CC2=CC3=CC4=CC5=CC=CC=C5C=C4C=C3C=C21 SLIUAWYAILUBJU-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
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- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
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- 229960005323 phenoxyethanol Drugs 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
- GDISDVBCNPLSDU-UHFFFAOYSA-N pyrido[2,3-g]quinoline Chemical compound C1=CC=NC2=CC3=CC=CN=C3C=C21 GDISDVBCNPLSDU-UHFFFAOYSA-N 0.000 description 1
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- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052702 rhenium Inorganic materials 0.000 description 1
- WUAPFZMCVAUBPE-UHFFFAOYSA-N rhenium atom Chemical compound [Re] WUAPFZMCVAUBPE-UHFFFAOYSA-N 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000005092 sublimation method Methods 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 238000001931 thermography Methods 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/10—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/10—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing aromatic rings
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- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/649—Aromatic compounds comprising a hetero atom
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
- C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
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- Y02E10/00—Energy generation through renewable energy sources
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- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to materials for use in electronic devices, in particular in organic electroluminescent devices, and to electronic devices, in particular organic electroluminescent devices, comprising these materials.
- OLEDs organic electroluminescent devices
- the structure of organic electroluminescent devices (OLEDs) in which organic semiconductors are employed as functional materials is described, for example, in US 4539507, US 5151629, EP 0676461 and WO 98/ 27136.
- the emitting materials employed here are increasingly organo- metallic complexes which exhibit phosphorescence instead of fluorescence.
- organometallic compounds as phosphorescence emitters.
- the properties of phosphorescent OLEDs are not only determined by the triplet emitters employed.
- the other materials used such as matrix materials, hole-blocking materials, electron-transport materials, hole-transport materials and electron- or exciton-blocking materials, are also of particular importance here. Improvements in these materials can thus also result in significant improvements in the OLED properties, particularly with respect to the efficiency, the lifetime and the thermal stability of the materials.
- the object of the present invention is the provision of compounds which are suitable for use in an OLED, in particular as matrix material for phosphorescent emitters, but also as hole-blocking material, as electron- transport material or optionally as a material for a charge generation layer.
- a further object of the present invention is to provide further organic semiconductors for organic electroluminescent devices so as to provide the person skilled in the art with a greater possible choice of materials for the production of OLEDs. It is known to use compounds with both non-spiro fluorenyl groups and triazinyl groups in OLEDs.
- US 7651790 discloses the use of OLEDs with a compound of the formula A-C-B where A is a hole- transporting group (including non-spiro fluorenyl groups among others), B is an electron-transporting group (including triazinyl groups among others) and C is a bond or linking group.
- A is a hole- transporting group (including non-spiro fluorenyl groups among others)
- B is an electron-transporting group (including triazinyl groups among others)
- C is a bond or linking group.
- WO 2010/015306 and WO 2005/053055 discloses OLEDs with fluorenes, including 9,9-(dimethyl or diphenyl) as well as bis-
- 9,9'-spiro- examples substituted in any position with nitrogen containing heterocycles including triazines and pyrimidines.
- WO 2015/073343 discloses OLEDs with triazine compounds substituted with at least two fluorenyl groups, one being a 9,9-diphenylfluorene.
- KR 2013115161 discloses OLEDs with a 1-triazinyl-9,9-dimethylfluorene where the triazine is substituted in the 4-position with 1-benzofuran and in the 6-position with a N-indene derivative.
- KR 2013061371 discloses OLEDs with a 1-(4-phenyl)triazinyl-9,9-dimethylfluorene derivative.
- US20100045170 describes OLEDs with a 1-(9-(10-(2-diazinyl)- anthracenyl)diazine)-9,9-dimethylfluorene.
- WO 2014/023388 discloses OLEDs with 9,9'-spiro- bifluorenes that are mono-substituted in the 1- or 4-positions with triazinyl or pyrimidinyl groups.
- WO 2011/006574 discloses OLEDs with 9,9'-spirobifluorenes that are di-substituted in the 4,4'- positions with triazinyl or pyrimidinyl groups.
- certain compounds described in greater detail below achieve this object, are highly suitable for use in OLEDs and result in improvements in the organic electroluminescent device.
- the improvements here relate, in particular, to the lifetime and/or the operating voltage.
- the present invention therefore relates to these compounds and to electronic devices, in particular organic electroluminescent devices, which comprise compounds of the type described below.
- the compounds of the invention are generally fluorene derivatives that are connected in one or more of the 1-, V-, 4-, or 4'- positions in any combination to a carbon atom of a triazinyl or pyrimidinyl derivative.
- the fluorene derivative of the invention uses the following numbering convention:
- the present invention relates to a compound of the formula (I),
- Zi and Z 2 are on each occurrence, identically or differently, H, D, F, CI, Br,
- P( 0)(Ri), SO, SO2, N(Ri)2, O, S or CON(Ri>2 and where one or more H atoms may be replaced by D, F, CI, Br, I, CN or NO2, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may in each case be substituted by one or more radicals Ri, or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals Ri.
- the fluorene derivatives of the invention are not bis-9,9'-spirobifluorenes; that is, the Zi and Z 2 groups at the 9-position do not represent another fluorene group.
- the heterocyclic substituted fluorene nucleus of the invention is not a derivative of:
- Zi and Z2 may form a spiro saturated ring system; for example, Zi and Z2 may represent a cyclopentyl or cyclohexyl ring system. However, it is preferred that Zi and Z 2 are separate substituents from each other and are not connected to each other at any point other than the 9- position of the fluorene nucleus.
- Yi and Y 2 are on each occurrence, identically or differently, D, F, CI, Br, I,
- An and Arc are on each occurrence, identically or differently, an aromatic or heteroaromatic ring system having 5 to 23 aromatic ring atoms, which may be substituted by one or more radicals Ri, preferably non-aromatic radicals Ri, with the proviso that a heteroaromatic ring system is
- L is on each occurrence, identically or differently, an aromatic or hetero- aromatic ring system having 5-30 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals Ri.
- a, b, c and d are each, identically or differently, 0 or 1 with the proviso that at least one of a, b, c or d is 1.
- e and f are each, identically or differently, 0, 1 , 2 or 3.
- n is on each occurrence, identically or differently, 0 or 1.
- the compound of formula (I) is not the following compound:
- an aryl group in the context of this invention contains from 6 to 24 carbon atoms; a heteroaryl group within the meaning of this invention containing from 2 to 24 carbon atoms and at least one heteroatom, with the proviso that the sum of carbon atoms and hetero atoms is at least 5.
- the heteroatoms are preferably selected from N, O and S.
- an aryl or heteroaryl group is either a simple aromatic ring, for example benzene, or a simple heteroaromatic ring, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl, such as naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc.
- an aromatic ring system in the sense of this invention contains from 6 to 40 carbon atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains 1 to 40 carbon atoms and at least one heteroatom in the ring system, with the proviso that the sum of carbon atoms and hetero atoms is at least 5.
- the heteroatoms are preferably selected from N, O and S.
- an aromatic or heteroaromatic ring system in the context of this invention is to be understood as a system that does not necessarily contain only aryl or heteroaryl groups, but in which a plurality of aryl or heteroaryl groups are connected by a non-aromatic moiety, such as, for example, a C, N or O atom or a carbonyl group.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, stilbene, etc.
- aromatic ring systems for the purposes of this invention.
- systems in which two or more aryl groups are connected for example, by a linear or cyclic alkyl group or by a silyl group.
- systems in which two or more aryl or heteroaryl groups are directly bonded to each other such, for example, biphenyl, terphenyl or quaterphenyl be understood unless indicated otherwise, also as an aromatic or heteroaromatic ring system.
- a cyclic alkyl, alkoxy or thioalkoxy means a monocyclic, bicyclic or an a polycyclic group.
- a C1 to C 40 alkyl group in which individual H atoms or CH2 groups may be substituted by the above-mentioned groups, include methyl, ethyl, n-propyl, i -propyl, cyclopropyl, n-butyl, i-butyl, s- butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, t-pentyl, 2-pentyl, neo-pentyl, cyclopentyl, n hexyl, s-hexyl, t-hexyl, 2-hexyl, 3-hexyl, neo- hexyl, cyclohexyl, 1-methylcyclopentyl, 2-methylpentyl, n-heptyl, 2-heptyl, 3-heptyl, 4-hept
- alkenyl group examples include ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl, cyclooctenyl or cyclooctadienyl.
- alkynyl group examples include, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl or octynyl.
- An alkoxy group having 1 to 40 C atoms is preferably taken to mean methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy,
- a thioalkyl group having 1 to 40 C atoms is taken to mean, in particular, methylthio, ethylthio, n-propylthio, i-propylthio, n-butylthio, i-butylthio, s-butylthio, t-butylthio, n-pentylthio, s-pentylthio, n-hexylthio, cyclohexylthio, n-heptyl- thio, cycloheptylthio, n-octylthio, cyclooctylthio, 2-ethylhexylthio, trifluoro- methylthio, pentafluoroethylthio, 2,2,2-trifluoroethylthi
- alkyl, alkoxy or thioalkyl groups in accordance with the present invention may be straight-chain, branched or cyclic, where one or more non-adjacent CH2 groups may be replaced by the above-mentioned groups; furthermore, one or more H atoms may also be replaced by D, F, CI, Br, I, CN or NO2, preferably F, CI or CN, further preferably F or CN, particularly preferably CN.
- an aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms which may be substituted with residues above yet and which can be linked via any position on the aromatic or heteroaromatic compounds, for example, groups are understood to be derived from benzene, naphthalene, anthracene, benzanthracene, phenanthrene, benzophenanthrene, pyrene, chrysene, perylene, fluoranthene, benzfluoranthen, naphthacene, pentacene, benzopyrene, biphenyl, biphenyl, terphenyl, fluorene, spirobifluorene, dihydro- phenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans- indeno- fluorene, cis- or frans-monobenzoindenofluorene, cis- or frans-di
- Ri refers to a first substituent and R2 is a further optional substituent on Ri as well on L, Zi, Z2, Yi and Y2 . Both Ri and R2 can be chosen independently from the same groups as described. Adjacent radicals or adjacent substituents in the sense of the present application are taken to mean substituents which are bonded to C atoms which are in turn bonded directly to one another or substituents which are bonded to the same C atom.
- the alkyl groups preferably have not more than five C atoms, particularly preferably not more than 4 C atoms, very particularly preferably not more than 1 C atom.
- suitable compounds are also those which are substituted by alkyl groups, in particular branched alkyl groups, having up to 10 C atoms or which are substituted by oligoarylene groups, for example ortho-, meta-, para- or branched terphenyl groups. It should be understood that for compounds that are processed by vacuum deposition, more than one compound can be co- evaporated at the same time to form a mixed layer. For example, a mixture of two or more different host compounds (one being a compound
- a mixed matrix layer with a light-emitting material
- two (or more) compounds can be separately evaporated and the resulting vapors mixed at the appropriate ratios to form a mixed layer.
- the compounds of the formula (I) or the preferred embodiments are used as matrix material for a phosphorescent emitter or in a layer which is directly adjacent to a phosphorescent layer, it is furthermore preferred for Ri, R2, Zi, Z2, Yi, Y2, An and Arc and L of the compound to contain no condensed aryl or heteroaryl groups in which more than two six-membered rings are condensed directly onto one another.
- Ri, R2, Zi, Z2, Yi, Y2 An and Arc and L of the compound to contain no condensed aryl or heteroaryl groups in which more than two six-membered rings are condensed directly onto one another.
- a triphenylene group which has more than two condensed six-membered rings, but is still suitable and preferred as a triplet matrix material. It is generally advantageous for the triplet energy of the compound used as a matrix material or in an adjacent layer to be the same or greater than the triplet energy of the phosphorescent material in the emitting layer.
- the compounds according to the invention described above in particular compounds which are substituted by reactive leaving groups, such as bromine, iodine, chlorine, boronic acid or boronic acid ester, or by reactive, polymerisable groups, such as olefins, styrenes, acrylates or oxetanes, can be used as monomers for the generation of corresponding oligomers, dendrimers or polymers.
- the oligomerisation or polymerisation here preferably takes place via the halogen functionality or the boronic acid functionality or via the polymerisable group. It is furthermore possible to crosslink the polymers via groups of this type.
- the compounds and polymers according to the invention can be employed as crosslinked or uncross- linked layer.
- the invention therefore furthermore relates to oligomers, polymers or den- drimers containing one or more of the compounds according to the invention indicated above, where one or more bonds from the compound according to the invention to the polymer, oligomer or dendrimer are present at one or more positions instead of substituents.
- this forms a side chain of the oligomer or polymer or is linked in the main chain or forms the core of a dendrimer.
- the polymers, oligomers or dendrimers may be conjugated, partially conjugated or non-conjugated.
- the oligomers or polymers may be linear, branched or dendritic. The same preferences as described above apply to the recurring units of the compounds according to the invention in oligomers, dendrimers and polymers.
- the monomers according to the invention are homopolymerised or copolymerised with further monomers. Preference is given to homopolymers or copolymers in which the units of the formula (I) or the preferred embodiments indicated above are present to the extent of 0.01 to 99.9 mol%, preferably 5 to 90 mol%, particularly preferably 20 to 80 mol%.
- Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (for example in accordance with EP 842208 or WO 2000/22026), spirobifluorenes (for example in accordance with EP 707020, EP 894107 or WO 2006/ 061181), para-phenylenes (for example in accordance with WO 92/18552), carbazoles (for example in accordance with WO 2004/070772 or
- the polymers, oligomers and dendrimers may also contain further units, for example electron-transport units.
- the polymers may contain triplet emitters, either copolymerised or mixed in as a blend.
- the combination of the oligomers, polymers or dendrimers according to the invention with triplet emitters leads to particularly good results.
- Q represents the triazine / pyrimidine subunit of Formula (I):
- Zi and Z2 groups in the 9-positions of the fluorene nucleus are, identically or differently, a straight-chain or branched alkyl group having 1 to 12 atoms, or an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms. More preferred are where Zi and Z2 are, identically or differently, a straight-chain alkyl group having 1 to 6 atoms, or an aromatic ring system having 6 to 24 aromatic ring atoms. Particularly preferred examples of alkyl groups include methyl and ethyl.
- aromatic ring systems are phenyl, p-t- butylphenyl, p-(heteroaromatic)phenyl, m- or -biphenyl or naphthyl. Of these, the most preferred are methyl or phenyl. While the Zi and Z2 groups may be the same or different, it is more preferred that they are identical. Some specific examples of suitable Zi and Z2 substituents on the fluorene nucleus of the compound of the invention include, but are not limited to:
- Yi and Y2 represents substituents on the two different rings of the fluorene nucleus of the compound of the invention. It should be understood that whenever a, b, c or d is 0 (no Q group), those positions may or may not be occupied by a Yi or Y2 group. Whenever e or f is 0, there are no Yi or Y2 substituents on that ring and the open positions are H. This is most preferred. Whenever e or f is not zero, Yi and Y2 are, identically or differently, preferred an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms.
- preferred aromatic groups include substituted or unsubstituted phenyl, naphthyl, or anthracenyl each of which may be further substituted by one or more Ri groups.
- preferred heteroaromatic groups include N-arylcarbazoyls, benzimidazoles, dibenzofurans, dibenzothiophenes or fluorenes, including 9,9'-spirobi- fluorenes. Whenever e or f is 2, it is furthermore preferred that two adjacent Yi or Y2 substituents form an annulated mono- or polycyclic, aliphatic or aromatic or heteroaromatic ring system with one another.
- Suitable Yi and Y2 substituents on the fluorene nucleus of the compound of the invention include, but are not limited to:
- Ri is as defined above and g may be
- the fluorene nucleus is substituted by one to four Q groups in the 1-, 1'-, 4-, 4'- positions in any combination. It is preferred that only one of a or b is 1 while only one of c or d is 1. It is even more preferred if b is 1 (a is 0) while either c or d is 1. It is still even more preferred that only one of a or b is 1 while c and d are both 0. It is most preferred that only b is 1 while a, c and d are 0.
- L is a linking group that connects (directly or indirectly) a carbon atom in a triazine or pyrimidine group to the fluorene nucleus.
- n 0, there is no linking group and the carbon atom of the triazine or pyrimidine group is directly attached to the fluorene nucleus by a single bond in the 1-, 1'-, 4- or 4'- position.
- a, b, c and d each is 1 and the
- n can be the same or different for each Q group.
- b and d are 1 (a and c are 0)
- corresponding n can be 0 and 1 as shown below:
- L is a linking group that indirectly connects a carbon atom in a triazine or pyrimidine group to any of the 1-, 1'-, 4- or 4'- positions of the fluorene nucleus through at least one other atom that isn't part of either the triazine / pyrimidine group or the fluorene nucleus.
- the connections of triazine / pyrimidine to L as well as L to the fluorene nucleus are both via single bonds.
- L is on each occurrence, identically or differently, an aromatic ring system having 6-30 aromatic ring atoms which may be further substituted.
- Some examples of preferred L groups are phenyl, biphenyl or anthracenyl. Of these, phenyl is most preferred, desirably via the 1 ,4- or 1 ,3-position of the phenyl. It is understood that L can be the same or different for each Q group; for example, in the following
- n 0.
- At least one X stands for N on each occurrence, identically or differently. In the sense of the invention, that means that for each Q group, at least one X is N in each heteroaromatic ring. When both X in a single ring are N, which is preferred, the Q group is a 2,4-disubstituted 1 ,3,5-triazine (triazinyl group):
- the Q group is a 2,4- disubstituted 1 ,5- or 1 ,3- pyrimidine (pyrimidinyl) group:
- the radicals Ri which are present on X do not form a ring with any adjacent substituents (An, Ar2, L or if n is 0, the fluorene nucleus or any Y substituents).
- the triazinyl or pyrimidinyl group is a single ring system and has no annulated rings. It is most preferred that Ri is H.
- a compound of Formula (I) may have 1 to 4 triazinyl groups, 1 to 4 pyrimidinyl groups or 1 to 4 groups in any combination of the two.
- the following compounds of Formula (I) where b and d are both 1 and a and c are both 0 and n is 0 for both Q groups illustrate that the Q may b
- aromatic or heteroaromatic ring systems having 5 to 23 aromatic ring atoms, which may in each case be substituted by one or more radicals Ri.
- the total of aromatic ring atoms (carbon or heteroatom) is the sum of all individual aromatic ring atoms (which includes for this purpose all sp 2 hybridized carbon atoms and divalent and trivalent heteroatoms when the heteroatoms are attached to at least two different sp 2 carbon atoms but excludes non-aromatic tetrahedral carbon and nitrogen atoms) within all aromatic groups in the substituent including Ri if present.
- suitable groups for An and Ar2 include benzene (6), ortho, meta- or para-biphenyl (12), ortho-, meta-, para- or branched terphenyl (18), 1-, 2-, 3- or 4- 9,9-dialkylfluorenyl (12), 1- or 2-naphthyl (10), pyrrole
- pyridazine (6) triazine (6), anthracene (14), phenanthrene (14), tri- phenylene (18), pyrene (16), benzanthracene (18), N-phenylphenanthridi- none (20) or combinations of two or three of these groups, each of which may be substituted by one or more radicals Ri, so long as there is no more than 23 aromatic ring atoms in total.
- Some examples of non-inventive sub- stituents with more than 23 aromatic ring atoms are quaterphenyl (24), 9,9- diphenylfluorene (24) and 9,9'-spirobifluorene (24).
- An and Ar2 particularly is selected from the group consisting of benzene, ortho-, meta- or para- biphenyl, ortho-, meta-, para- or branched terphenyl, naphthyl, tri- phenylene, 9,9-dialkylfluorenyl or derivatives, N-phenylcarbazole, dibenzo- furan and dibenzothiophene. It should be understood that this preferred group includes not only the basic unsubstituted structures but also includes derivatives thereof, such as those substituted with further Ri substituents.
- 9,9-dialkylfluorenyl, N-phenylcarbazole, dibenzofuran and dibenzothiophene derivatives can have annulated rings or be connected through a linking phenyl group to Q so long as there are 23 or less aromatic ring atoms in the entire substituent including any aromatic ring atoms in Ri. It is preferred that any Ri susbtituents on An and Ar2 are non-aromatic.
- An and Ar2 are connected to the triazinyl or pyrimidinyl groups via one single bond and do not form a ring system or have any other connection to the triazinyl or pyrimidinyl groups.
- An and Arc are different from the linking group L; that is, the triazinyl or pyrimidinyl group is not connected to the fluorene through An or Ar2.
- An and Ar2 are identical.
- the aromatic groups in the groups An and Ar2 are not para-linked, i.e. they are preferably not para-biphenyl or para-terphenyl, but instead, for example, the respective ortho- or mefa-linked structures.
- an or Ar2 (or both) is or contains a nitrogen containing hetero- aromatic group such as a carbazole, pyrrole, imidazole or benzimidazole group
- the heteroaromatic group is not to be linked via a nitrogen atom directly to the triazine or pyrimidine nucleus, but instead via a carbon atom of the heteroaromatic group to a carbon atom in the triazine or pyrimidine.
- An or Ar2 is a N-phenylcarbazole group, it can be connected to the triazine or pyrimidine nucleus via a carbon atom of the carbazole or a carbon atom of the N-phenyl group (as shown in the examples below) but if An or Ar2 is a carbazole group, it should not be connected to the triazine or pyrimidine nucleus directly by the nitrogen atom of the carbazole group.
- An and Arc include:
- formulations of the compounds according to the invention are necessary. These formulations can be, for example, solutions, dispersions or emulsions. It may be preferred to use mixtures of two or more solvents for this purpose.
- Suitable and preferred solvents are, for example, toluene, anisole, o-, m- or p-xylene, methyl benzoate, mesitylene, tetraline, veratrole, THF, methyl- THF, THP, chlorobenzene, dioxane, phenoxytoluene, in particular 3- phenoxytoluene, (-)-fenchone, 1 ,2,3,5-tetramethylbenzene, 1 ,2,4,5-tetra- methylbenzene, 1-methylnaphthalene, 2-methylbenzothiazole, 2-phenoxy- ethanol, 2-pyrrolidinone, 3-methylanisole, 4-methylanisole, 3,4-dimethyl- anisole, 3,5-dimethylanisole, acetophenone, a-terpineol, benzothiazole, butyl benzoate, cumene, cyclohexanol, cyclohexanone, cyclohex
- the present invention therefore furthermore relates to a formulation comprising a compound according to the invention and at least one further compound.
- the further compound may be, for example, a solvent, in particular one of the above-mentioned solvents or a mixture of these solvents.
- the further compound may also be at least one further organic or inorganic compound which is likewise employed in the electronic device, for example an emitting compound and/or a further matrix material. Suitable emitting compounds and further matrix materials are indicated below in connection with the organic electroluminescent device.
- This further compound may also be polymeric.
- the compounds according to the invention are suitable for use in an electronic device, in particular in an organic electroluminescent device.
- the present invention therefore furthermore relates to the use of a compound according to the invention in an electronic device, in particular in an organic electroluminescent device.
- the present invention still furthermore relates to an electronic device comprising at least one compound
- An electronic device in the sense of the present invention is a device which comprises at least one layer which comprises at least one organic compound.
- the component may also comprise inorganic materials or also layers which are built up entirely from inorganic materials.
- the electronic device is preferably selected from the group consisting of organic electroluminescent devices (OLEDs), organic integrated circuits (O-ICs), organic field-effect transistors (O-FETs), organic thin-film transistors (O-TFTs), organic light-emitting transistors (O-LETs), organic solar cells (O-SCs), dye-sensitised organic solar cells (DSSCs), organic optical detectors, organic photoreceptors, organic field-quench devices (O-FQDs), light- emitting electrochemical cells (LECs), organic laser diodes (O-lasers) and "organic plasmon emitting devices”, but preferably organic electroluminescent devices (OLEDs), particularly preferably phosphorescent OLEDs.
- OLEDs organic electroluminescent devices
- the organic electroluminescent device comprises cathode, anode and at least one emitting layer. Apart from these layers, it may also comprise further layers, for example in each case one or more hole-injection layers, hole-transport layers, hole-blocking layers, electron-transport layers, electron-injection layers, exciton-blocking layers, electron-blocking layers and/or charge-generation layers. Interlayers, which have, for example, an exciton-blocking function, may likewise be introduced between two emitting layers. However, it should be pointed out that each of these layers does not necessarily have to be present.
- the organic electroluminescent device here may comprise one emitting layer, or it may comprise a plurality of emitting layers.
- a plurality of emission layers are present, these preferably have in total a plurality of emission maxima between 380 nm and 750 nm, resulting overall in white emission, i.e. various emitting compounds which are able to fluoresce or phosphoresce are used in the emitting layers.
- various emitting compounds which are able to fluoresce or phosphoresce are used in the emitting layers.
- Particular preference is given to systems having two emitting layers, where the two layers exhibit blue and orange or yellow emission, or three emitting layers, where the three layers exhibit blue, green and orange or red emission (for the basic structure see, for example,
- the organic electroluminescent device according to the invention may also be a tandem OLED, in particular also for white- emitting OLEDs.
- the compound according to the invention in accordance with the embodiments indicated above can be employed in various layers of the electronic device, depending on the precise structure. Preference is given to an organic electroluminescent device comprising a compound of the formula (I) or the preferred embodiments indicated above as matrix material for phosphorescent or fluorescent emitters, in particular for phosphorescent emitters, and/or in an electron-blocking or exciton-blocking layer and/or in a charge generation layer and/or in a hole-blocking or electron-transport layer, depending on the precise substitution.
- the compound according to the invention is employed as matrix material for a phosphorescent compound in an emitting layer.
- the organic electroluminescent device here may comprise one emitting layer, or it may comprise a plurality of emitting layers, where at least one emitting layer comprises at least one compound according to the invention as matrix material.
- the compound according to the invention is employed as matrix material for a phosphorescent compound in an emitting layer, it is preferably employed in combination with one or more phosphorescent materials (triplet emitters).
- Phosphorescence in the sense of this invention is taken to mean the luminescence from an excited state having relatively high spin multiplicity, i.e. a spin state > 1 , in particular from an excited triplet state.
- all luminescent complexes containing transition metals or lanthanides, in particular all iridium, platinum and copper complexes are to be regarded as phosphorescent compounds.
- the mixture of the compound according to the invention and the emitting compound comprises between 99 and 1% by vol., preferably between 98 and 10% by vol., particularly preferably between 97 and 60% by vol., in particular between 95 and 80% by vol., of the compound according to the invention, based on the entire mixture comprising emitter and matrix material.
- the mixture comprises between 1 and 99% by vol., preferably between 2 and 90% by vol., particularly preferably between 3 and 40% by vol., in particular between 5 and 20% by vol., of the emitter, based on the entire mixture comprising emitter and matrix material.
- a further preferred embodiment of the present invention is the use of the compound according to the invention as matrix material for a phosphorescent emitter in combination with a further matrix material.
- Particularly suitable matrix materials which can be employed in combination with the compounds according to the invention are aromatic ketones, aromatic phos- phine oxides or aromatic sulfoxides or sulfones, for example in accordance with WO 2004/013080, WO 2004/093207, WO 2006/005627 or WO 2010/ 006680, triarylamines, carbazole derivatives, for example CBP (N,N-bis- carbazolylbiphenyl) or the carbazole derivatives disclosed in WO 2005/ 039246, US 2005/0069729, JP 2004/288381 , EP 1205527, WO 2008/ 086851 or WO 2013/041176, indolocarbazole derivatives, for example in accordance with WO 2007/063754 or WO 2008/056746, indenocarbazole derivatives
- a further phosphorescent emitter which emits at shorter wavelength than the actual emitter may likewise be present in the mixture as co-host, or a compound which does not participate in the charge transport to a significant extent, if at all, as described, for example, in WO 20 0/108579. It is well within the art to select appropriate matrix materials and emitters for light-emitting layers along with determining the appropriate relative proportions of all the materials present.
- the phosphorescence emitters used are preferably compounds which contain copper, molybdenum, tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, in particular compounds which contain iridium or platinum.
- the compounds according to the invention are also suitable, in particular, as matrix materials for phosphorescent emitters in organic electroluminescent devices, as described, for example, in US 2011/0248247 and
- the organic electroluminescent device according to the invention does not comprise a separate hole- injection layer and/or hole-transport layer and/or hole-blocking layer and/or electron-transport layer, i.e. the emitting layer is directly adjacent to the hole-injection layer or the anode, and/or the emitting layer is directly adjacent to the electron-transport layer or the electron-injection layer or the cathode, as described, for example, in WO 2005/053051. It is furthermore possible to use a metal complex which is the same as or similar to the metal complex in the emitting layer as hole-transport or hole-injection material directly adjacent to the emitting layer, as described, for example, in WO 2009/030981.
- the compound according to the invention is employed in an exciton-blocking layer.
- the compound according to the invention is employed as electron-transport material in an electron-transport or electron-injection layer.
- the emitting layer here may be fluorescent or phosphorescent. If the compound is employed as electron-transport material, it may be preferred for it to be doped, for example with alkali metals or alkali-metal complexes, such as, for example, Li or LiQ (lithium hydroxyquinolinate).
- the compound according to the invention is employed in a hole-blocking layer.
- a hole- blocking layer is taken to mean a layer which is directly adjacent to an emitting layer on the cathode side.
- Another preferred embodiment is employing the compound as part of a charge generation layer.
- a charge generation layer (CGL) works as an injector of an electron-hole pair upon voltage application and is well-known in the art.
- a CGL consists of a electron-rich layer (for example, a n-doped electron transporting layer) adjacent to an electron-poor layer (for example, a p-doped hole transporting layer).
- the CGL can be only a single layer. In other cases, one or both layers of the CGL may or may not be doped.
- an organic electroluminescent device characterised in that one or more layers are coated by means of a sublimation process, in which the materials are applied by vapour deposition in vacuum sublimation units at an initial pressure of less than 10 '5 mbar, preferably less than 10 "6 mbar.
- the initial pressure it is also possible for the initial pressure to be even lower, for example less than 10 ⁇ 7 mbar.
- an organic electroluminescent device characterised in that one or more layers are coated by means of the OVPD (organic vapour phase deposition) process or with the aid of carrier-gas sublimation, in which the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
- OVPD organic vapour phase deposition
- carrier-gas sublimation in which the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
- OVJP organic vapour jet printing
- an organic electroluminescent device characterised in that one or more layers are produced from solution, such as, for example, by spin coating, or by means of any desired printing process, such as, for example, screen printing, flexographic printing, offset printing, LITI (light induced thermal imaging, thermal transfer printing), ink- jet printing or nozzle printing.
- Soluble compounds which are obtained, for example, by suitable substitution, are necessary for this purpose.
- hybrid processes in which, for example, one or more layers are applied from solution and one or more further layers are applied by vapour deposition.
- These processes are generally known to the person skilled in the art and can be applied by him without inventive step to organic electroluminescent devices comprising the compounds according to the invention.
- the compounds according to the invention and the organic electroluminescent devices according to the invention are distinguished by one or more of the following surprising advantages over the prior art:
- the compounds according to the invention employed as matrix material for fluorescent or phosphorescent emitters, result in long lifetimes. This applies, in particular, if the compounds are employed as matrix material for a phosphorescent emitter.
- the compounds are employed as matrix material for a phosphorescent emitter or as a hole-blocking material.
- compounds are employed as matrix material for a phosphorescent emitter or in an electron-transport layer.
- the materials of the invention can generally be prepared according to the following synthetic scheme 1 (Note: In Scheme 1 , two or three X will be N and for when there are two nitrogens, the other X will be CRi and R3 is preferably, but is not limited to, the fluorene skeleton; in some
- the fluorene skeleton may be added in step 1 or 2a/b):
- Step 1 295g (1.6mol, 1.0eq) of 2,4,6-trichloro-1 ,3,5-triazine [108-77-0] 1 are solved in 800ml dried THF in a four-necked flask under an inert atmosphere. The solution is cooled with an ice bath to about 0°C and 800ml (1.6mol, 1.0eq) of a 2mol/l phenylmagnesiumchloride solution are added slowly to maintain the temperature below 10°C. Then, the mixture is stirred at room temperature overnight and after the reaction had finished, 800ml of toluene and 1.2L of HCI 2% are added. The organic phase is separated, extracted three times with water and dried over sodium sulfate. The solvent is evaporated under reduced pressure until the product precipitates. After washing the solid with ethanol, 242g (1.1mol, 67%) of the desired product 3a are obtained.
- Step 2a 1 5g (61mmol, 1.12eq) of magnesium turnings are heated in a four-necked flask for a few minutes. Then, a few ml of 19g (60mmol, 1.10eq) of 1-Bromo-3,5-diphenylbenzene [103068-20-8] in 100ml dried THF were added until the Grignard reaction starts. Then, the solution was added slowly to maintain the Grignard reaction at reflux. After the addition is complete, the mixture was cooled to about 0°C with an ice bath.
- Step 2b 35g (150mmol, 1.0eq) 2,4-Dichloro-6-phenyl-[1,3,5]triazine, 35g (150mmol, 1.0eq) dibenzothiophene-4-boronic acid [108847-20-7] and 18g (170mmol, 1.1 Oeq) sodium carbonate are dissolved in 300ml 1 ,4-dioxane, 300ml water and 120ml toluene under an inert atmosphere. Then, 1.8g (1.5mmol, 0.01 eq) tetrakis(triphenylphosphine)palladium is added and the mixture refluxed over night at 110°C.
- Step 3b 30g (80mmol, 1.0eq) of 7a, 21g (88mmol, 1.1eq) 9,9-Dimethyl- 9H-fluoren-4-yl-boronic acid [1246022-50-3] and 17g (160mmol, 2.0eq) sodium carbonate are dissolved in 400ml toluene, 250ml water and 170ml ethanol under an inert atmosphere. Then, 0.93g (0.80mmol, 0.01eq) tetrakis(triphenylphosphine)palladium is added and the mixture refluxed over night at 110°C. After the reaction is completed, 300ml water were added and the precipitated (36g) solid is filtered.
- the present invention furthermore relates to a process for the preparation of a compound of the formula (I), comprising the reaction steps of:
- V1-V7 and E1-E22 show data from various OLEDs.
- Substrate pre-treatment of examples V1-V7 and E1-E22 Glass plates with structured ITO (50 nm, indium tin oxide) are coated with 20 nm
- PEDOTPSS Poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate), CLEVIOSTM PVP Al 4083 from Heraeus Precious Metals GmbH Germany, spin-coated from a water-based solution) and form the substrates on which the OLEDs are processed.
- the OLEDs have in principle the following layer structure: substrate / hole- transport layer (HTL) / optional interlayer (IL) / electron-blocking layer
- EBL emission layer
- EML emission layer
- HBL hole-blocking layer
- ETL electron-transport layer
- EIL electron-injection layer
- the emission layer here always consists of at least one matrix material (host material) and an emitting dopant (emitter), which is admixed with the matrix material or matrix materials in a certain proportion by volume by co-evaporation.
- An expression such as IC1 :M1 :TEG1
- the electron-transport layer may also consist of a mixture of two materials.
- the OLEDs are characterised by standard methods.
- the electroluminescence spectra, the current efficiency (CE1000, measured in cd/A at 1000 cd/m 2 ), the luminous efficacy (LE1000, measured in Im/W at 1000 cd/m 2 ), the external quantum efficiency (EQE1000, measured in % at 1000 cd/m 2 ) and the voltage (U1000, measured at 1000 cd/m 2 in V) are determined from current/ voltage/luminance characteristic lines (IUL characteristic lines) assuming a Lambertian emission profile.
- the electroluminescence (EL) spectra are recorded at a luminous density of
- the lifetime is determined.
- the lifetime is defined as the time after which the luminous density has dropped to a certain proportion from a certain initial luminous density Li when the OLED is driven at a constant current.
- the device data of various OLEDs is summarized in Table 2.
- the examples V1-V7 are comparison examples according to the state-of-the- art.
- the examples E1-E22 show data of inventive OLEDs.
- inventive compounds as electron transport layer and host material in phosphorescent OLEDs
- inventive compounds as electron transport layer and as host material results in significantly improved OLED device data compared to state-of-the-art materials, especially with respect to device lifetime.
- inventive materials (1) and (187) in an ETL mixed with LiQ results in improved LT compared to devices with the materials CE1 and CE2 (comparison of example V1 and V2 with E1 and E3, respectively).
- inventive compound (186) which is identical to CE3 except it is a 4-(9,9-dimethylfluorenyl)triazine results in a significant improvement in LT efficacy when tested as a host in triplet green OLEDs (see V3 vs E2).
- CE6 which is a 4- (9,9-dimethylfluorene)triazine with a 9,9'-spirobifluorene substituent on the triazine hardly gives any improvement compared to CE1 (sample V1) which is like CE6 but where a phenyl replaces the 4-(9,9-dimethylfluorene) group on the triazine.
- V7 SpA1 HATCN SpMA1 (CE7):TEG1 ST2:LiQ
Abstract
Description
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Citations (90)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
WO1992018552A1 (en) | 1991-04-11 | 1992-10-29 | Wacker-Chemie Gmbh | Conductive polymers with conjugated double bonds |
EP0652273A1 (en) | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organic material for electroluminescent device and electroluminescent device |
EP0676461A2 (en) | 1994-04-07 | 1995-10-11 | Hoechst Aktiengesellschaft | Spiro compounds and their application as electroluminescence materials |
EP0707020A2 (en) | 1994-10-14 | 1996-04-17 | Hoechst Aktiengesellschaft | Conjugated polymers with a spiro atom and their use as electroluminescent materials |
EP0842208A1 (en) | 1995-07-28 | 1998-05-20 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
WO1998027136A1 (en) | 1996-12-16 | 1998-06-25 | Aventis Research & Technologies Gmbh & Co Kg | ARYL-SUBSTITUTED POLY(p-ARYLENE VINYLENES), METHOD FOR THE PRODUCTION AND USE THEREOF IN ELECTROLUMINESCENT COMPONENTS |
EP0894107A1 (en) | 1996-04-17 | 1999-02-03 | Hoechst Research & Technology Deutschland GmbH & Co. KG | Polymers with spiro atoms and their use as electroluminescent materials |
WO2000022026A1 (en) | 1998-10-10 | 2000-04-20 | Celanese Ventures Gmbh | Conjugated polymers containing special fluorene structural elements with improved properties |
EP1028136A2 (en) | 1999-02-10 | 2000-08-16 | Carnegie-Mellon University | A method of forming poly-(3-substituted) thiophenes |
WO2000070655A2 (en) | 1999-05-13 | 2000-11-23 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
US6225467B1 (en) | 2000-01-21 | 2001-05-01 | Xerox Corporation | Electroluminescent (EL) devices |
US6229012B1 (en) | 1998-10-01 | 2001-05-08 | Xerox Corporation | Triazine compositions |
WO2001041512A1 (en) | 1999-12-01 | 2001-06-07 | The Trustees Of Princeton University | Complexes of form l2mx as phosphorescent dopants for organic leds |
WO2002002714A2 (en) | 2000-06-30 | 2002-01-10 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
EP1191614A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device and metal coordination compound therefor |
EP1191613A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device, display apparatus and metal coordination compound |
EP1191612A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device, display apparatus and metal coordination compound |
EP1205527A1 (en) | 2000-03-27 | 2002-05-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
WO2004013080A1 (en) | 2002-08-01 | 2004-02-12 | Covion Organic Semiconductors Gmbh | Spirobifluorene derivatives, their preparation and uses thereof |
WO2004041901A1 (en) | 2002-11-08 | 2004-05-21 | Covion Organic Semiconductors Gmbh | Aryl-substituted polyindenofluorenes for use in organic electroluminiscent devices |
US20040147742A1 (en) | 2003-01-21 | 2004-07-29 | Wong Ken Tsung | Pyrimidine spirobifluorene oligomer for organic light-emitting device |
WO2004070772A2 (en) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Conjugated polymers and blends containing carbazole, representation and use thereof |
JP2004288381A (en) | 2003-03-19 | 2004-10-14 | Konica Minolta Holdings Inc | Organic electroluminescent element |
WO2004093207A2 (en) | 2003-04-15 | 2004-10-28 | Covion Organic Semiconductors Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
US6821643B1 (en) | 2000-01-21 | 2004-11-23 | Xerox Corporation | Electroluminescent (EL) devices |
WO2004113412A2 (en) | 2003-06-23 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Polymer |
WO2004113468A1 (en) | 2003-06-26 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Novel materials for electroluminescence |
WO2005011013A1 (en) | 2003-07-21 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
WO2005014689A2 (en) | 2003-08-12 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Conjugated polymers containing dihydrophenanthrene units and use thereof |
WO2005019373A2 (en) | 2003-08-19 | 2005-03-03 | Basf Aktiengesellschaft | Transition metal complexes comprising carbene ligands serving as emitters for organic light-emitting diodes (oled's) |
US20050069729A1 (en) | 2003-09-30 | 2005-03-31 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
WO2005033244A1 (en) | 2003-09-29 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Metal complexes |
WO2005040302A1 (en) | 2003-10-22 | 2005-05-06 | Merck Patent Gmbh | New materials for electroluminescence and the utilization thereof |
WO2005053051A1 (en) | 2003-11-25 | 2005-06-09 | Merck Patent Gmbh | Organic electroluminescent element |
WO2005053055A1 (en) | 2003-11-27 | 2005-06-09 | Merck Patent Gmbh | Organic electroluminescent element |
WO2005104264A1 (en) | 2004-04-26 | 2005-11-03 | Merck Patent Gmbh | Electroluminescent polymers and use therof |
WO2005111172A2 (en) | 2004-05-11 | 2005-11-24 | Merck Patent Gmbh | Novel material mixtures for use in electroluminescence |
US20050258742A1 (en) | 2004-05-18 | 2005-11-24 | Yui-Yi Tsai | Carbene containing metal complexes as OLEDs |
JP2005347160A (en) | 2004-06-04 | 2005-12-15 | Konica Minolta Holdings Inc | Organic electroluminescent element, lighting device, and display device |
EP1617710A1 (en) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
WO2006005627A1 (en) | 2004-07-15 | 2006-01-19 | Merck Patent Gmbh | Oligomeric derivatives of spirobifluorene, their preparation and use |
WO2006061181A1 (en) | 2004-12-06 | 2006-06-15 | Merck Patent Gmbh | Partially conjugated polymers, their representation and their use |
WO2006117052A1 (en) | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organic electroluminescent device and boric acid and borinic acid derivatives used therein |
EP1731584A1 (en) | 2004-03-31 | 2006-12-13 | Konica Minolta Holdings, Inc. | Organic electroluminescent device material, organic electroluminescent device, display and illuminating device |
WO2007017066A1 (en) | 2005-08-10 | 2007-02-15 | Merck Patent Gmbh | Electroluminescent polymers and use thereof |
WO2007063754A1 (en) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
WO2007137725A1 (en) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | New materials for organic electroluminescent devices |
WO2008056746A1 (en) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
WO2008086851A1 (en) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Carbazole derivatives for organc electroluminescent devices |
WO2009030981A2 (en) | 2006-12-28 | 2009-03-12 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
WO2009062578A1 (en) | 2007-11-12 | 2009-05-22 | Merck Patent Gmbh | Organic electroluminescent devices comprising azomethine-metal complexes |
WO2010006680A1 (en) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
US7651790B2 (en) | 2004-11-05 | 2010-01-26 | Samsung Mobile Display Co., Ltd. | Organic light-emitting device |
WO2010015306A1 (en) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh, | Organic electroluminescence device |
US20100045170A1 (en) | 2008-04-02 | 2010-02-25 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2010054729A2 (en) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2010054730A1 (en) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Organic electroluminescent devices |
WO2010086089A1 (en) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metal complexes |
WO2010108579A1 (en) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organic electroluminescent device |
WO2010136109A1 (en) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011000455A1 (en) | 2009-06-30 | 2011-01-06 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2011006574A1 (en) | 2009-07-14 | 2011-01-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011042107A2 (en) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011057706A2 (en) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materials for electronic devices |
WO2011060877A2 (en) | 2009-11-17 | 2011-05-26 | Merck Patent Gmbh | Materials for organic light emitting devices |
WO2011060859A1 (en) | 2009-11-17 | 2011-05-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011060867A1 (en) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Nitrogen-containing condensed heterocyclic compounds for oleds |
WO2011088877A1 (en) | 2010-01-25 | 2011-07-28 | Merck Patent Gmbh | Compounds for electronic devices |
US20110248247A1 (en) | 2010-04-09 | 2011-10-13 | Sony Corporation | Organic el display unit, method of manufacturing the same, and solution used in method |
WO2011157339A1 (en) | 2010-06-15 | 2011-12-22 | Merck Patent Gmbh | Metal complexes |
WO2012007086A1 (en) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metal complexes |
WO2012048781A1 (en) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Triphenylene-based materials for organic electroluminescent devices |
US20120223633A1 (en) | 2011-03-04 | 2012-09-06 | Sony Corporation | Organic el display device and method of manufacturing the same |
WO2012143080A2 (en) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2012163471A1 (en) | 2011-06-03 | 2012-12-06 | Merck Patent Gmbh | Metal complexes |
WO2013000531A1 (en) | 2011-06-28 | 2013-01-03 | Merck Patent Gmbh | Metal complexes |
WO2013020631A1 (en) | 2011-08-10 | 2013-02-14 | Merck Patent Gmbh | Metal complexes |
WO2013041176A1 (en) | 2011-09-21 | 2013-03-28 | Merck Patent Gmbh | Carbazole derivatives for organic electroluminescence devices |
WO2013056776A1 (en) | 2011-10-20 | 2013-04-25 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20130061371A (en) | 2011-12-01 | 2013-06-11 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
KR20130115161A (en) | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
WO2014008982A1 (en) | 2012-07-13 | 2014-01-16 | Merck Patent Gmbh | Metal complexes |
WO2014023388A1 (en) | 2012-08-10 | 2014-02-13 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2014023377A2 (en) | 2012-08-07 | 2014-02-13 | Merck Patent Gmbh | Metal complexes |
WO2015073343A1 (en) | 2013-11-12 | 2015-05-21 | Dow Global Technologies Llc | Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same |
KR101537500B1 (en) * | 2014-04-04 | 2015-07-20 | 주식회사 엘지화학 | Organic light emitting diode |
WO2015153633A2 (en) * | 2014-03-31 | 2015-10-08 | Parker-Hannifin Corporation | Wearable robotic device |
Family Cites Families (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100537499B1 (en) | 2002-07-26 | 2005-12-19 | 삼성전자주식회사 | Method of generating transmission control parameter and selective retranmission method according to the packet characteristics. |
KR100730140B1 (en) * | 2005-07-15 | 2007-06-19 | 삼성에스디아이 주식회사 | A triazine-based compound and an organic light emitting device employing the same |
WO2011021689A1 (en) | 2009-08-21 | 2011-02-24 | 東ソー株式会社 | Cyclic azine derivatives, processes for producing these, and organic electroluminescent element containing these as component |
WO2012150826A1 (en) | 2011-05-03 | 2012-11-08 | Rohm And Haas Electronic Materials Korea Ltd. | Novel organic electroluminescent compounds and an organic electroluminescent device using the same |
WO2013012298A1 (en) * | 2011-07-21 | 2013-01-24 | Rohm And Haas Electronic Materials Korea Ltd. | 9h-carbazole compounds and electroluminescent devices involving them |
US9391281B2 (en) * | 2012-07-13 | 2016-07-12 | Lg Chem, Ltd. | Heterocyclic compound and organic electronic element containing same |
KR102388354B1 (en) | 2013-12-19 | 2022-04-19 | 메르크 파텐트 게엠베하 | Heterocyclic spiro compounds |
KR20150074603A (en) | 2013-12-24 | 2015-07-02 | 희성소재 (주) | Fluorene-based compound and organic light emitting device using the same |
CN104795503B (en) | 2014-01-16 | 2018-07-20 | 三星显示有限公司 | Organic light emitting apparatus |
KR101537499B1 (en) | 2014-04-04 | 2015-07-16 | 주식회사 엘지화학 | Organic light emitting diode |
KR101542714B1 (en) | 2014-04-04 | 2015-08-12 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting device comprising the same |
KR102255197B1 (en) | 2014-05-02 | 2021-05-25 | 삼성디스플레이 주식회사 | Organic light emitting device |
KR102178087B1 (en) | 2014-07-03 | 2020-11-12 | 덕산네오룩스 주식회사 | Compound for organic electronic element, organic electronic element using the same, and an electronic device thereof |
KR101772746B1 (en) | 2014-08-12 | 2017-08-30 | 주식회사 엘지화학 | Organic light emitting diode |
KR101560102B1 (en) | 2014-11-20 | 2015-10-13 | 주식회사 엘지화학 | Organic light emitting device |
KR20160111780A (en) | 2015-03-17 | 2016-09-27 | 주식회사 엘지화학 | Organic light emitting device |
KR101593368B1 (en) | 2015-04-22 | 2016-02-11 | 주식회사 엘지화학 | Hetero-cyclic compound and organic light emitting diode comprising the same |
-
2016
- 2016-07-01 WO PCT/EP2016/001117 patent/WO2017016630A1/en active Application Filing
- 2016-07-01 EP EP23202035.4A patent/EP4301110A3/en active Pending
- 2016-07-01 KR KR1020187005481A patent/KR20180031766A/en not_active Application Discontinuation
- 2016-07-01 CN CN201680044327.6A patent/CN107922359A/en active Pending
- 2016-07-01 US US15/748,437 patent/US11098019B2/en active Active
- 2016-07-01 EP EP16734191.6A patent/EP3328841B1/en active Active
- 2016-07-01 JP JP2018504890A patent/JP6839697B2/en active Active
- 2016-07-27 TW TW105123770A patent/TWI707845B/en active
- 2016-07-27 TW TW111109932A patent/TW202225147A/en unknown
- 2016-07-27 TW TW109134170A patent/TWI761977B/en active
-
2021
- 2021-02-12 JP JP2021021129A patent/JP7121817B2/en active Active
-
2022
- 2022-08-05 JP JP2022125716A patent/JP2022166114A/en active Pending
Patent Citations (92)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4539507A (en) | 1983-03-25 | 1985-09-03 | Eastman Kodak Company | Organic electroluminescent devices having improved power conversion efficiencies |
WO1992018552A1 (en) | 1991-04-11 | 1992-10-29 | Wacker-Chemie Gmbh | Conductive polymers with conjugated double bonds |
US5151629A (en) | 1991-08-01 | 1992-09-29 | Eastman Kodak Company | Blue emitting internal junction organic electroluminescent device (I) |
EP0652273A1 (en) | 1993-11-09 | 1995-05-10 | Shinko Electric Industries Co. Ltd. | Organic material for electroluminescent device and electroluminescent device |
EP0676461A2 (en) | 1994-04-07 | 1995-10-11 | Hoechst Aktiengesellschaft | Spiro compounds and their application as electroluminescence materials |
EP0707020A2 (en) | 1994-10-14 | 1996-04-17 | Hoechst Aktiengesellschaft | Conjugated polymers with a spiro atom and their use as electroluminescent materials |
EP0842208A1 (en) | 1995-07-28 | 1998-05-20 | The Dow Chemical Company | 2,7-aryl-9-substituted fluorenes and 9-substituted fluorene oligomers and polymers |
EP0894107A1 (en) | 1996-04-17 | 1999-02-03 | Hoechst Research & Technology Deutschland GmbH & Co. KG | Polymers with spiro atoms and their use as electroluminescent materials |
WO1998027136A1 (en) | 1996-12-16 | 1998-06-25 | Aventis Research & Technologies Gmbh & Co Kg | ARYL-SUBSTITUTED POLY(p-ARYLENE VINYLENES), METHOD FOR THE PRODUCTION AND USE THEREOF IN ELECTROLUMINESCENT COMPONENTS |
US6229012B1 (en) | 1998-10-01 | 2001-05-08 | Xerox Corporation | Triazine compositions |
WO2000022026A1 (en) | 1998-10-10 | 2000-04-20 | Celanese Ventures Gmbh | Conjugated polymers containing special fluorene structural elements with improved properties |
EP1028136A2 (en) | 1999-02-10 | 2000-08-16 | Carnegie-Mellon University | A method of forming poly-(3-substituted) thiophenes |
WO2000070655A2 (en) | 1999-05-13 | 2000-11-23 | The Trustees Of Princeton University | Very high efficiency organic light emitting devices based on electrophosphorescence |
WO2001041512A1 (en) | 1999-12-01 | 2001-06-07 | The Trustees Of Princeton University | Complexes of form l2mx as phosphorescent dopants for organic leds |
US6225467B1 (en) | 2000-01-21 | 2001-05-01 | Xerox Corporation | Electroluminescent (EL) devices |
US6821643B1 (en) | 2000-01-21 | 2004-11-23 | Xerox Corporation | Electroluminescent (EL) devices |
EP1205527A1 (en) | 2000-03-27 | 2002-05-15 | Idemitsu Kosan Co., Ltd. | Organic electroluminescence device |
WO2002002714A2 (en) | 2000-06-30 | 2002-01-10 | E.I. Du Pont De Nemours And Company | Electroluminescent iridium compounds with fluorinated phenylpyridines, phenylpyrimidines, and phenylquinolines and devices made with such compounds |
WO2002015645A1 (en) | 2000-08-11 | 2002-02-21 | The Trustees Of Princeton University | Organometallic compounds and emission-shifting organic electrophosphorescence |
EP1191614A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device and metal coordination compound therefor |
EP1191613A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device, display apparatus and metal coordination compound |
EP1191612A2 (en) | 2000-09-26 | 2002-03-27 | Canon Kabushiki Kaisha | Luminescence device, display apparatus and metal coordination compound |
WO2004013080A1 (en) | 2002-08-01 | 2004-02-12 | Covion Organic Semiconductors Gmbh | Spirobifluorene derivatives, their preparation and uses thereof |
WO2004041901A1 (en) | 2002-11-08 | 2004-05-21 | Covion Organic Semiconductors Gmbh | Aryl-substituted polyindenofluorenes for use in organic electroluminiscent devices |
US20040147742A1 (en) | 2003-01-21 | 2004-07-29 | Wong Ken Tsung | Pyrimidine spirobifluorene oligomer for organic light-emitting device |
WO2004070772A2 (en) | 2003-02-06 | 2004-08-19 | Covion Organic Semiconductors Gmbh | Conjugated polymers and blends containing carbazole, representation and use thereof |
JP2004288381A (en) | 2003-03-19 | 2004-10-14 | Konica Minolta Holdings Inc | Organic electroluminescent element |
WO2004093207A2 (en) | 2003-04-15 | 2004-10-28 | Covion Organic Semiconductors Gmbh | Mixtures of matrix materials and organic semiconductors capable of emission, use of the same and electronic components containing said mixtures |
EP1617710A1 (en) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Material for organic electroluminescent device, organic electroluminescent device, illuminating device and display |
EP1617711A1 (en) | 2003-04-23 | 2006-01-18 | Konica Minolta Holdings, Inc. | Organic electroluminescent device and display |
WO2004113412A2 (en) | 2003-06-23 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Polymer |
WO2004113468A1 (en) | 2003-06-26 | 2004-12-29 | Covion Organic Semiconductors Gmbh | Novel materials for electroluminescence |
WO2005011013A1 (en) | 2003-07-21 | 2005-02-03 | Covion Organic Semiconductors Gmbh | Organic electroluminescent element |
WO2005014689A2 (en) | 2003-08-12 | 2005-02-17 | Covion Organic Semiconductors Gmbh | Conjugated polymers containing dihydrophenanthrene units and use thereof |
WO2005019373A2 (en) | 2003-08-19 | 2005-03-03 | Basf Aktiengesellschaft | Transition metal complexes comprising carbene ligands serving as emitters for organic light-emitting diodes (oled's) |
WO2005033244A1 (en) | 2003-09-29 | 2005-04-14 | Covion Organic Semiconductors Gmbh | Metal complexes |
WO2005039246A1 (en) | 2003-09-30 | 2005-04-28 | Konica Minolta Holdings, Inc. | Organic electroluminescent device, illuminating device, and display |
US20050069729A1 (en) | 2003-09-30 | 2005-03-31 | Konica Minolta Holdings, Inc. | Organic electroluminescent element, illuminator, display and compound |
WO2005040302A1 (en) | 2003-10-22 | 2005-05-06 | Merck Patent Gmbh | New materials for electroluminescence and the utilization thereof |
WO2005053051A1 (en) | 2003-11-25 | 2005-06-09 | Merck Patent Gmbh | Organic electroluminescent element |
WO2005053055A1 (en) | 2003-11-27 | 2005-06-09 | Merck Patent Gmbh | Organic electroluminescent element |
EP1731584A1 (en) | 2004-03-31 | 2006-12-13 | Konica Minolta Holdings, Inc. | Organic electroluminescent device material, organic electroluminescent device, display and illuminating device |
WO2005104264A1 (en) | 2004-04-26 | 2005-11-03 | Merck Patent Gmbh | Electroluminescent polymers and use therof |
WO2005111172A2 (en) | 2004-05-11 | 2005-11-24 | Merck Patent Gmbh | Novel material mixtures for use in electroluminescence |
US20050258742A1 (en) | 2004-05-18 | 2005-11-24 | Yui-Yi Tsai | Carbene containing metal complexes as OLEDs |
JP2005347160A (en) | 2004-06-04 | 2005-12-15 | Konica Minolta Holdings Inc | Organic electroluminescent element, lighting device, and display device |
WO2006005627A1 (en) | 2004-07-15 | 2006-01-19 | Merck Patent Gmbh | Oligomeric derivatives of spirobifluorene, their preparation and use |
US7651790B2 (en) | 2004-11-05 | 2010-01-26 | Samsung Mobile Display Co., Ltd. | Organic light-emitting device |
WO2006061181A1 (en) | 2004-12-06 | 2006-06-15 | Merck Patent Gmbh | Partially conjugated polymers, their representation and their use |
WO2006117052A1 (en) | 2005-05-03 | 2006-11-09 | Merck Patent Gmbh | Organic electroluminescent device and boric acid and borinic acid derivatives used therein |
WO2007017066A1 (en) | 2005-08-10 | 2007-02-15 | Merck Patent Gmbh | Electroluminescent polymers and use thereof |
WO2007063754A1 (en) | 2005-12-01 | 2007-06-07 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent element and organic electroluminescent element |
WO2007137725A1 (en) | 2006-05-31 | 2007-12-06 | Merck Patent Gmbh | New materials for organic electroluminescent devices |
WO2008056746A1 (en) | 2006-11-09 | 2008-05-15 | Nippon Steel Chemical Co., Ltd. | Compound for organic electroluminescent device and organic electroluminescent device |
WO2009030981A2 (en) | 2006-12-28 | 2009-03-12 | Universal Display Corporation | Long lifetime phosphorescent organic light emitting device (oled) structures |
WO2008086851A1 (en) | 2007-01-18 | 2008-07-24 | Merck Patent Gmbh | Carbazole derivatives for organc electroluminescent devices |
WO2009062578A1 (en) | 2007-11-12 | 2009-05-22 | Merck Patent Gmbh | Organic electroluminescent devices comprising azomethine-metal complexes |
US20100045170A1 (en) | 2008-04-02 | 2010-02-25 | Gracel Display Inc. | Novel organic electroluminescent compounds and organic electroluminescent device using the same |
WO2010006680A1 (en) | 2008-07-18 | 2010-01-21 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2010015306A1 (en) | 2008-08-08 | 2010-02-11 | Merck Patent Gmbh, | Organic electroluminescence device |
WO2010054729A2 (en) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2010054730A1 (en) | 2008-11-11 | 2010-05-20 | Merck Patent Gmbh | Organic electroluminescent devices |
WO2010086089A1 (en) | 2009-02-02 | 2010-08-05 | Merck Patent Gmbh | Metal complexes |
WO2010108579A1 (en) | 2009-03-23 | 2010-09-30 | Merck Patent Gmbh | Organic electroluminescent device |
WO2010136109A1 (en) | 2009-05-29 | 2010-12-02 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011000455A1 (en) | 2009-06-30 | 2011-01-06 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2011006574A1 (en) | 2009-07-14 | 2011-01-20 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011042107A2 (en) | 2009-10-08 | 2011-04-14 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011057706A2 (en) | 2009-11-14 | 2011-05-19 | Merck Patent Gmbh | Materials for electronic devices |
WO2011060877A2 (en) | 2009-11-17 | 2011-05-26 | Merck Patent Gmbh | Materials for organic light emitting devices |
WO2011060859A1 (en) | 2009-11-17 | 2011-05-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2011060867A1 (en) | 2009-11-18 | 2011-05-26 | Merck Patent Gmbh | Nitrogen-containing condensed heterocyclic compounds for oleds |
WO2011088877A1 (en) | 2010-01-25 | 2011-07-28 | Merck Patent Gmbh | Compounds for electronic devices |
US20110248247A1 (en) | 2010-04-09 | 2011-10-13 | Sony Corporation | Organic el display unit, method of manufacturing the same, and solution used in method |
WO2011157339A1 (en) | 2010-06-15 | 2011-12-22 | Merck Patent Gmbh | Metal complexes |
WO2012007086A1 (en) | 2010-07-16 | 2012-01-19 | Merck Patent Gmbh | Metal complexes |
WO2012048781A1 (en) | 2010-10-15 | 2012-04-19 | Merck Patent Gmbh | Triphenylene-based materials for organic electroluminescent devices |
US20120223633A1 (en) | 2011-03-04 | 2012-09-06 | Sony Corporation | Organic el display device and method of manufacturing the same |
WO2012143080A2 (en) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
WO2012163471A1 (en) | 2011-06-03 | 2012-12-06 | Merck Patent Gmbh | Metal complexes |
WO2013000531A1 (en) | 2011-06-28 | 2013-01-03 | Merck Patent Gmbh | Metal complexes |
WO2013020631A1 (en) | 2011-08-10 | 2013-02-14 | Merck Patent Gmbh | Metal complexes |
WO2013041176A1 (en) | 2011-09-21 | 2013-03-28 | Merck Patent Gmbh | Carbazole derivatives for organic electroluminescence devices |
WO2013056776A1 (en) | 2011-10-20 | 2013-04-25 | Merck Patent Gmbh | Materials for organic electroluminescent devices |
KR20130061371A (en) | 2011-12-01 | 2013-06-11 | 롬엔드하스전자재료코리아유한회사 | Novel organic electroluminescence compounds and organic electroluminescence device using the same |
KR20130115161A (en) | 2012-04-10 | 2013-10-21 | 에스에프씨 주식회사 | Heterocyclic com pounds and organic light-emitting diode including the same |
WO2014008982A1 (en) | 2012-07-13 | 2014-01-16 | Merck Patent Gmbh | Metal complexes |
WO2014023377A2 (en) | 2012-08-07 | 2014-02-13 | Merck Patent Gmbh | Metal complexes |
WO2014023388A1 (en) | 2012-08-10 | 2014-02-13 | Merck Patent Gmbh | Materials for organic electroluminescence devices |
WO2015073343A1 (en) | 2013-11-12 | 2015-05-21 | Dow Global Technologies Llc | Compositions containing fluorene substituted triazine derived compounds, and electronic devices containing the same |
WO2015153633A2 (en) * | 2014-03-31 | 2015-10-08 | Parker-Hannifin Corporation | Wearable robotic device |
KR101537500B1 (en) * | 2014-04-04 | 2015-07-20 | 주식회사 엘지화학 | Organic light emitting diode |
Non-Patent Citations (3)
Title |
---|
DATABASE CAPLUS [online] CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; 23 July 2015 (2015-07-23), XP002760867, Database accession no. 2015:1199479 * |
M. S. ARNOLD ET AL., APPL. PHYS. LETT., vol. 92, 2008, pages 053301 |
WU, APPL. PHYS. LETT., vol. 81, no. 4, pages 577 - 592 |
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US11706977B2 (en) | 2018-01-11 | 2023-07-18 | Samsung Electronics Co., Ltd. | Heterocyclic compound, composition including the same, and organic light-emitting device including the heterocyclic compound |
JP2019119723A (en) * | 2018-01-11 | 2019-07-22 | 三星電子株式会社Samsung Electronics Co.,Ltd. | Compound, organic electroluminescent element material, organic electroluminescent element composition, and organic electroluminescent element |
CN113383054A (en) * | 2019-01-17 | 2021-09-10 | 默克专利有限公司 | Material for organic electroluminescent device |
WO2021162122A1 (en) | 2020-02-14 | 2021-08-19 | Idemitsu Kosan Co., Ltd. | Compound, material for an organic electroluminescence device and an organic electroluminescence device comprising the compound |
KR20230138466A (en) | 2021-01-29 | 2023-10-05 | 이데미쓰 고산 가부시키가이샤 | Compounds, materials for organic electroluminescent devices, organic electroluminescent devices and electronic devices |
WO2022243403A1 (en) | 2021-05-21 | 2022-11-24 | Merck Patent Gmbh | Method for the continuous purification of at least one functional material and device for the continuous purification of at least one functional material |
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KR20180031766A (en) | 2018-03-28 |
JP7121817B2 (en) | 2022-08-18 |
JP6839697B2 (en) | 2021-03-10 |
TWI761977B (en) | 2022-04-21 |
US20180222872A1 (en) | 2018-08-09 |
JP2022166114A (en) | 2022-11-01 |
US11098019B2 (en) | 2021-08-24 |
TW201718526A (en) | 2017-06-01 |
JP2021098707A (en) | 2021-07-01 |
TW202225147A (en) | 2022-07-01 |
CN107922359A (en) | 2018-04-17 |
JP2018531883A (en) | 2018-11-01 |
TW202124366A (en) | 2021-07-01 |
TWI707845B (en) | 2020-10-21 |
EP4301110A2 (en) | 2024-01-03 |
EP4301110A3 (en) | 2024-04-10 |
EP3328841B1 (en) | 2023-10-11 |
EP3328841A1 (en) | 2018-06-06 |
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